Sodium Methoxide → Sodium Iodide

HRID 1801417Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1801417
[I-:1].[OH:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([C:10]2[C:15]([CH3:16])=[CH:14][N+:13]([CH3:17])=[CH:12][C:11]=2[CH3:18])=[C:5]([CH3:19])[CH:4]=1.C[O-].[Na+:22]>CO>[CH3:9][C:7]1[C:6](=[C:10]2[C:11]([CH3:18])=[CH:12][N:13]([CH3:17])[CH:14]=[C:15]2[CH3:16])[C:5]([CH3:19])=[CH:4][C:3](=[O:2])[CH:8]=1.[Na+:22].[I-:1]

Komponenten

5

Edukt 2

HCID 10942334Sodium MethoxideHCID 669936364-(4-Hydroxy-2,6-dimethyl-phenyl)-1,3,5-trimethyl-pyridinium iodide

Produkt 2

HCID 5238Sodium IodideAusbeute 98 %HCID 669933403,5-dimethyl-4-(1,3,5-trimethyl-1H-pyridin-4-ylidene)-cyclohexa-2,5-dienone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To the methylpyridinium iodide salt 7 (0.184 g, 0.500 mmol) was added dropwise a solution of sodium methoxide in methanol (1.2 mL, 0.5 M). The color of the mixture immediately changed from yellow to red. After stirring at room temperature for 10 min, the solvent was removed under reduced pressure. The resulting solid was then recrystallized from anhydrous methanol/THF to afford the orange title compound as a complex with NaI (0.382 g, 98%): 1H NMR (400 MHz, DMSO-d6): δ 8.818 (s, 2H), 5.983 (s, 2H), 4.265 (s, 3H), 2.055 (s, 6H), 1.566 (s, 6H); 13C NMR (100 MHz, DMSO-d6): δ 161.235, 142.173, 137.851, 132.019, 118.598, 114.039, 46.917, 19.574, 16.754; MS (ESI): m/z 242.4 [(M+H)+,100]; HRMS (EI): m/z 241.1463 [M+]; calcd, 241.1467. Anal. Calcd. for C16H19NO.NaI: C, 49.12; H, 4.90; N, 3.58. Found; C, 49.04; H, 5.40; N, 3.49.

Aufarbeitung

  1. customthe solvent was removed under reduced pressure
  2. customThe resulting solid was then recrystallized from anhydrous methanol/THF

Quellen und Nachweise

ORD-Eintrag
ord-711200ebfcc64004ba60ff4814ccf88e
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08349222B2

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